Hydrochloric Acid → HCID 10126802, compound

HRID 900964Notes

Reaction equation

HRID 900964 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:10]2=[N:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=[C:9]2[C:8]([CH2:17][C:18]2[S:19][C:20]3[C:26]([F:27])=[CH:25][C:24]([F:28])=[C:23]([F:29])[C:21]=3[N:22]=2)=[CH:7]1)C.[OH-].[Na+].Cl>COCCOC>[CH2:15]([C:12]1[N:11]=[C:10]2[N:6]([CH2:5][C:4]([OH:30])=[O:3])[CH:7]=[C:8]([CH2:17][C:18]3[S:19][C:20]4[C:26]([F:27])=[CH:25][C:24]([F:28])=[C:23]([F:29])[C:21]=4[N:22]=3)[C:9]2=[CH:14][CH:13]=1)[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59698774HCID 59698774, compound

Product 1

HCID 10126802HCID 10126802, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of [6-ethyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid ethyl ester (0.474 g, 1.10 mmol) and BHT (2 mg) in 1,2-dimethoxyethane (10 mL, 1 M) is cooled to 0° C. and treated with 1 N NaOH (5 mL, 5 mmol). After stirring 30 min, the soln is acidified to pH 3-4 with 1 N HCl and extracted with ethyl acetate (3×). The combined organic layers are washed with saturated aq NaCl, dried over MgSO4 and filtered through a layered pad of celite, charcoal and florisil to give [6-ethyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid (0.25 g, 56%). mp 155-157° C.; Rf 0.63 (50% methanol in chloroform) 1H NMR (DMSO-d6, 300 MHz) δ 12.98 (br s, 1 H), 7.87 (d, J=8.1 Hz, 1 H), 7.73-7.64 (m, 1 H), 7.53 (s, 1 H), 6.98 (d, J=8.1 Hz, 1 H), 4.99 (s, 2 H), 4.64 (s, 2 H), 2.76 (q, J=7.8 Hz, 2 H), 1.21 (t, J=7.8 Hz, 3 H); LRMS calcd for C19H14F3N3O2S: 405.4; found 405.0 (M)+. Anal. Calcd for C19H14F3N3O2S: C, 56.29; H, 3.48; N, 10.37; S, 7.91. Found C, 56.12; H, 3.40; N, 10.27; S, 7.91.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers are washed with saturated aq NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through a layered pad of celite, charcoal and florisil

Sources & evidence

ORD record
ord-24a6d29635a1421ba4d5477adc188ef1
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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